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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:47:55 UTC
Update Date2017-10-23 19:15:45 UTC
HMDB IDHMDB0060658
Secondary Accession Numbers
  • HMDB60658
  • HMDB60978
Metabolite Identification
Common NameCarbamazepine-10,11-epoxide
DescriptionCarbamazepine-10,11-epoxide is a metabolite of carbamazepine. Carbamazepine (CBZ) is an anticonvulsant and mood-stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder, as well as trigeminal neuralgia. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
10,11-EpoxycarbamazepineChEBI
Carbamazepine 10,11-oxideChEBI
Carbamazepine epoxideChEBI
Carbamazepine 10,11-epoxideMeSH
Carbamazepine epoxide, 1a-(13)C-labeledMeSH
Chemical FormulaC15H12N2O2
Average Molecular Weight252.268
Monoisotopic Molecular Weight252.089877638
IUPAC Name3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
Traditional Name3-oxa-11-azatetracyclo[10.4.0.0²,⁴.0⁵,¹⁰]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
CAS Registry Number36507-30-9
SMILES
NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12
InChI Identifier
InChI=1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)
InChI KeyZRWWEEVEIOGMMT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • Carbonic acid derivative
  • Urea
  • Dialkyl ether
  • Oxirane
  • Ether
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP1.58ALOGPS
logP1.97ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.86 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.98 m³·mol⁻¹ChemAxon
Polarizability25.61 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2090000000-1c00887035045a46e64cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-0090000000-ecf7de18b8b6dca8e574View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01q9-0960000000-baaab3735118a6815d95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-5f960cbf9a2cc6167270View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-7ae96bba0545f7a49d65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-f5d9e3256a5025c053f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01p9-0090000000-b4a8017bc5a22029286aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-92d916d85c6bfb1c8c8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ei-0390000000-8b6d0377758bc766aecaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01q9-0950000000-54f4932e8819ef33fc59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0910000000-f98fd081a308fa16c768View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-8b69c7ac8b048b7d3892View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-c63c11ed10e957dca130View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-623298bbf57b289b1282View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ei-0390000000-b77b3aa6c369fd8b0818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0950000000-32d3a419a11e5ffcd132View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0910000000-72c13fa6ddd8b27641e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-d4ce4b02188dd4b58833View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-c2ed076d4e592ce2f653View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-b5886f3f5846ab71f72dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-af9f413b6f446d69709fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0090000000-10bc18215ee3ab2ba1ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p6-8690000000-a0c1e51c6cec85694c4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k96-5090000000-ecc2f07a1eefb2949d89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3090000000-19d6ac25e86c1e0a6a84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9320000000-a52f23fc0b4f15a7d389View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Carbamazepine Metabolism PathwayPw000610Pw000610 greyscalePw000610 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00291
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC07496
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID3388
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Wei CY, Chung WH, Huang HW, Chen YT, Hung SI: Direct interaction between HLA-B and carbamazepine activates T cells in patients with Stevens-Johnson syndrome. J Allergy Clin Immunol. 2012 Jun;129(6):1562-9.e5. doi: 10.1016/j.jaci.2011.12.990. Epub 2012 Feb 8. [PubMed:22322005 ]
      2. McKauge L, Tyrer JH, Eadie MJ: Factors influencing simultaneous concentrations of carbamazepine and its epoxide in plasma. Ther Drug Monit. 1981;3(1):63-70. [PubMed:7233491 ]